Efficient synthesis of ESI-09, a novel non-cyclic nucleotide EPAC antagonist

Tetrahedron Letters

Volumn 54, Issue 12, 2013, Pages 1546-1549

  Chen, Haijun ^a   Ding, Chunyong ^a   Wild, Christopher ^a   Liu, Huiling ^a   Wang, Tianzhi ^a   White, Mark A ^a   Cheng, Xiaodong ^a   Zhou, Jia ^a  

^a University of Texas Medical Branch School of Medicine   (United States)

Author keywords

Cyanomethyl ketone; EPAC antagonist; ESI 09; Isoxazole; Modified Kowalski's protocol

Indexed keywords

CYCLIC AMP; ESI 09; EXCHANGE PROTEIN DIRECTLY ACTIVATED BY CAMP 1; ISOXAZOLE; PROTEIN INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; DRUG POTENCY; DRUG SPECIFICITY; DRUG SYNTHESIS;

EID: 84873716320     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.01.024     Document Type: Article

References (26)

1. D. Hariharan, A. Saied, and H.M. Kocher HPB (Oxford) 10 2008 58
2. A.F. Hezel, A.C. Kimmelman, B.Z. Stanger, N. Bardeesy, and R.A. Depinho Genes Dev. 20 2006 1218
3. M. Hidalgo N. Engl. J. Med. 362 2010 1605
4. J. de Rooij, F.J. Zwartkruis, M.H. Verheijen, R.H. Cool, S.M. Nijman, A. Wittinghofer, and J.L. Bos Nature 396 1998 474
5. H. Kawasaki, G.M. Springett, N. Mochizuki, S. Toki, M. Nakaya, M. Matsuda, D.E. Housman, and A.M. Graybiel Science 282 1998 2275
6. G.G. Holz, O.G. Chepurny, and F. Schwede Cell. Signal. 20 2008 10
7. M. Gloerich, and J.L. Bos Annu. Rev. Pharmacol. Toxicol. 50 2010 355
8. M. Grandoch, S.S. Roscioni, and M. Schmidt Br. J. Pharmacol. 159 2010 265
9. M. Breckler, M. Berthouze, A.C. Laurent, B. Crozatier, E. Morel, and F. Lezoualc'h Cell. Signal. 23 2011 1257
10. R. Lorenz, T. Aleksic, M. Wagner, G. Adler, and C.K. Weber Pancreas 37 2008 102
11. T. Tsalkova, F.C. Mei, and X. Cheng PLoS ONE 7 2012 e30441
12. T. Tsalkova, F.C. Mei, S. Li, O.G. Chepurny, C.A. Leech, T. Liu, G.G. Holz, V.L. Woods Jr., and X. Cheng Proc. Natl. Acad. Sci. U.S.A. 109 2012 18613
13. H. Chen, T. Tsalkova, F.C. Mei, Y. Hu, X. Cheng, and J. Zhou Bioorg. Med. Chem. Lett. 22 2012 4038
14. M. Almahariq, T. Tsalkova, F.C. Mei, H. Chen, J. Zhou, S.K. Sastry, F. Schwede, and X. Cheng Mol. Pharmacol. 83 2013 122
15. R.M. Abdel-Motaleb, A.A. Makhloof, H.M. Ibrahim, and M.H. Elnagdi J. Heterocycl. Chem. 43 2006 931
16. S.I. Aziz, H.F. Anwar, D.H. Fleita, and M.H. Elnagdi J. Heterocycl. Chem. 44 2007 725
17. H.M.E. Hassaneen Synth. Commun. 37 2007 3579
18. H. Behbehani, H.M. Ibrahim, S. Makhseed, and H. Mahmoud Eur. J. Med. Chem. 46 2011 1813
19. S. Arseniyadis, K.S. Kyler, and D.S. Watt Org. React. (N.Y.) 31 1984 1
20. A.R. Katritzky, A.A.A. Abdel-Fattah, and M. Wang J. Org. Chem. 68 2003 4932
21. Y. Ji, W.C. Trenkle, and J.V. Vowles Org. Lett. 8 2006 1161
22. T.M.V.D. PinhoeMelo Curr. Org. Chem. 9 2005 925
23. F. Lepage, F. Tombret, G. Cuvier, A. Marivain, and J.M. Gillardin Eur. J. Med. Chem. 27 1992 581
24. C.J. Kowalski, and M.S. Haque J. Org. Chem. 50 1985 5140
25. E.D. Soli, A.S. Manoso, M.C. Patterson, P. DeShong, D.A. Favor, R. Hirschmann, and A.B. Smith III J. Org. Chem. 64 1999 3171
26. The crystallographic data have been deposited in full at the Cambridge Crystallographic Data Centre, reference CCDC 913321, accessible at http://www.ccdc.cam.ac.uk.